179107-93-8

Basic information

• Product Name: 4-broMo-5-((4-hydroxyphenethylaMino)Methyl)-2-Methoxyphenol
• Synonyms: 4-broMo-5-((4-hydroxyphenethylaMino)Methyl)-2-Methoxyphenol
• CAS NO: 179107-93-8
• Molecular Formula: C₁₆H₁₈BrNO₃
• Molecular Weight: 352.22302
• Mol File: 179107-93-8.mol

Chemical Properties

• Boiling Point: 503.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.435±0.06 g/cm3(Predicted)
• PKA: 8.88±0.23(Predicted)
• CAS DataBase Reference: 4-broMo-5-((4-hydroxyphenethylaMino)Methyl)-2-Methoxyphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-broMo-5-((4-hydroxyphenethylaMino)Methyl)-2-Methoxyphenol(179107-93-8)
• EPA Substance Registry System: 4-broMo-5-((4-hydroxyphenethylaMino)Methyl)-2-Methoxyphenol(179107-93-8)

Safety Data

• Hazardous Substances Data: 179107-93-8(Hazardous Substances Data)

Upstream product

• 51-67-2 tyrosamine 
• 2973-59-3 2-bromoisovanillin 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 621-59-0 isovanillin 

Downstream Products

• 122584-18-3 N-(4-hydroxyphenethyl)-N-(2-bromo-5-hydroxy-4-methoxybenzyl)formamide 
• 296237-44-0 N-(2-bromo-5-hydroxy-4-methoxybenzyl)-N-(4-hydroxyphenethyl)trifluoroacetamide 
• 510-77-0 (4aS,8aS)-rel-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-one 
• 510-77-0 (-)-narwedine 
• 1953-04-4 Galantamine hydrobromide 
• 13062-78-7 N-[2-(4-hydroxyphenyl)ethyl]formamide 
• 2973-59-3 2-bromoisovanillin 
• 51-67-2 tyrosamine 
• 122584-14-9 N-formyl-1-bromo-narwedine 
• 188822-63-1 N-(2-bromo-5-hydroxy-4-methoxybenzyl)-N-(4-hydroxyphenethyl)methylamine 

Relevant articles and documents

Biomimetic synthesis of galantamine: Via laccase/TEMPO mediated oxidative coupling

Laccase-mediated intramolecular oxidative radical coupling of N-formyl-2-bromo-O-methylnorbelladine afforded a novel and isolable spirocyclohexadienonic intermediate of galantamine. High yield and conversion of substrate were obtained in the presence of the redox mediator 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO). This laccase procedure, with an overall yield of 34%, represents a scalable and environmentally friendly alternative to previously reported syntheses of galantamine based on the use of potassium ferricyanide as an unspecific radical coupling reagent.

Synthesis, biological evaluation and molecular modeling studies of substitutedN-benzyl-2-phenylethanamines as cholinesterase inhibitors

In this work, we report the synthesis of a series of derivatives ofN-benzyl-2-phenylethanamine which is the framework of norbelladine, the natural common precursor of the Amaryllidaceae alkaloids. These compounds were assessed in the inhibition of both AChE and BChE which are the enzymes responsible for the breakdown of acetylcholine and hence they constitute targets in the palliative treatment of Alzheimer's disease. In particular, brominated derivatives exhibited the lowest IC50values against AChE. Interestingly, the presence of iodine in one of the aromatic rings highly increased the inhibition of BChE compared to its analogues, with an IC50value similar to that of galantamine, which is the reference compound currently used in the treatment of AD. A possible mechanism of action for these compounds was determined by molecular modeling studies using combined techniques of docking and molecular dynamics simulations.

Processes for the preparation of derivatives of 4a, 5, 9, 10, 11, 12-hexahydro-6H-benzofuro-[3a, 3, 2-ef][2]benzazepine

The invention relates to processes for the preparation of 4a,5,9,10,11,12-hexahydro-6H-benzofuro[3a,3,2-ef][2]benzazepine, or derivatives thereof. Furthermore, the invention also relates to the compounds formed during the preparation of 4a, 5,9,10,11,12-hexahydro-6H-benzofuro[3a,3,2-ef][2]benzazepine.

New achievements in the field of intramolecular phenolic coupling reactions, using hypervalent (III) iodine reagent: Synthesis of galanthamine

Our investigations on the Oxidative possibilities of the hypervalent iodine(III) reagent established that phenyliodine(III)bis(trifluoroacctate (PIFA) can provide one-pot contiguous coupling-cyclization reaction giving a product with narwedine skeleton, when used in a phenolic coupling reaction of p'-bromonorbelladine derivatives. A suitably selected precursor gave up to 60% yield of the coupled product.

Development of a pilot scale process for the anti-alzheimer drug (-)-galanthamine using large-scale phenolic oxidative coupling and crystallisation-induced chiral conversion

(-)-Galanthamine has been synthesised using an efficient nine-step procedure, which in large scale affords 12.4 (6.7-19.1)% overall yield. The process improvements and optimization of each step are described. Notable steps include (i) an oxidative phenol coupling and (ii) crystallisation-induced chiral conversion of (±)-narwedine to (-)-narwedine. This is a practical and cost-effective synthesis of (-)-galanthamine which is amenable to pilot plant scale-up to afford sufficient material for use in clinical trials.

New kilogram-synthesis of the anti-Alzheimer drug (-)-galanthamine

A concise, scalable synthesis of (-)-galanthamine, a drug being used for the treatment of Alzheimer's disease, is described. The yield of the critical phenolic coupling step was optimized to 45-50%. For the reduction of the aryl bromide, air-activated LiAlH4 was used and racemic narwedine was converted to (-)-narwedine by a second order asymmetric transformation.